Locations in Chicago and the North Shore of Chicago that rent Sailboats, Kayaks and Jet Skis Chicago, IL Chicago Sailing Belmont Harbor 3400 N. LSD off of Recreation Drive “B” Dock Boats: J/22's, J/24's J/30,T-10, J/34, J/105, Hunter-326 Chicago Jet Ski Rentals: Jet Ski Chicago North Ave Beach, 1600 LSD, Chicago IL Windy City Watersports Montrose Beach, 4400 LSD, Chicago IL Evanston, IL Dempster/Greenwood Beach Evanston Park District Boats: Barnett 1400's, Lasers and Sunfish) and kayaks Northwestern Sailing Center 2311 Campus Drive Evanston, IL 60208 Boats: Laser-class sailboats, 420-class sailboats, Windsurfing boards with rigs, Hobie 16, Hobie Wave, Hobie Getaway, Stand up Paddleboards, Single & Double Kayaks Wilmette, IL Gilson Beach Wilmette Park District Lake St at Lake Michigan Boats: Hobie Getaways, Hobie Waves, Sunfish, Single & Double Seat Kayak Free at Last Charters "Free at Last" is our 42-foot, two-masted 27,000 lb. ketch sailboat available for charter out of Wilmette Harbor on the North Shore of Chicago. FreeAtLastCharters.com Glencoe, IL Glencoe Park District Park Ave at Lake Michigan Boats: Barnett 1400, Kayaks Waukegan, IL Chicago Sailing - Waukegan  Waukegan Harbor Next to Larsen Marine